Homeschool programs for high school ask more of parents than many expect, but differently than the early years did. Courtney Sanford has lived this from both sides as a Classical Conversations mom and co-author of Marvelous to Behold, a book woven into the Challenge curriculum.
In this article, she describes how the parent’s role shifts from instructor to mentor, what that looks like with great books and big conversations, and how it prepares students to lead long after the academic year ends. Oliver Wendell Holmes Jr. put it this way:
“Once the mind has been stretched by a new idea, it will never again return to its original size.”
The Challenge years are when the stretching begins.
What Is the CC Challenge Program?
The Classical Conversations Challenge program is a classical Christian homeschool curriculum for students ages 12 and up. Organized into six levels (Challenge A through Challenge IV), it uses a Socratic seminar approach to help students engage with great books, develop the Fifteen Skills of Learning, and grow as independent thinkers and future leaders. Students meet weekly in a learning community led by a Tutor while parents remain the primary educators throughout the academic year.
The Challenge programs are appropriately named: they are a challenge. They provide many opportunities for students to do great things, push themselves further than they thought they could go, and step outside their comfort zones.
The Parent’s Role Changes in High School: And That’s a Good Thing
Even though you may drop off your students at their Challenge classes, you should not “drop out” of the job of being the teacher. Your role changes from that of the steady coach of Foundations’ memory work to being a mentor and advisor to your students. The shift is significant, and it opens something richer than lesson delivery. You are being invited deeper into your student’s intellectual and character formation.
What Leigh Bortins Teaches Us About Questions and Conversations
Leigh Bortins has written the essential companion guides for this season of education. In The Question, she equips parents to teach with questions rather than answers, drawing on the Five Common Topics of dialectic to build curiosity and strengthen the relationship between parents and students. Learning to ask well is the first movement of mentoring.
The second movement is learning to stay. In The Conversation, the third book in Leigh’s Trivium Trilogy, she makes a compelling case for parents to remain engaged throughout the high school years rather than stepping back as the work grows more difficult. Thirty years of homeschooling inform her conviction: conversations through the rhetoric arts strengthen family bonds, provide accountability for good habits, and guide students toward virtuous adulthood. They are the roadmap for the Challenge years.
Become the Keeper of the Books: Preserving Timeless Truths for Timely Problems
How to Have Meaningful Conversations About the Challenge Books
If you are not engaging in great conversations about literature, history, science, theology, and current events with your Challenge student, you are missing something irreplaceable. The books for Challenge are wisely chosen, and each one opens a door.
Bring these conversations to the dinner table so that the whole family can listen and participate. Dads especially enjoy these topics. The powerful combination of the Challenge books, your student’s Tutor, and the essay assignments will set you up for discussions that go far beyond academics and give you the priceless opportunity to mentor your child, not just in the study of literature, but in the development of character and the formation of a leader.
Find out Why Are We Reading This Challenge A Literature?
Challenge A and B: Character, Self-Reliance, and the Big Ideas
In Challenge A and B, you will notice that the books have an emphasis on character: the values of hard work, self-reliance, and overcoming challenges. These are qualities your student will need to succeed in Challenge, in college, and in all of life. Challenge A and B rhetoric books also provide substantial food for thought. The ideas of origins are deep and complex and should spark many great conversations at home.
Carry On, Mr. Bowditch is one such book, and it offers a clear picture of what Challenge Tutors are cultivating in students. The main character, Nat Bowditch, was born into poverty during the American Revolution, became an indentured servant, and yet managed to self-educate in navigation, astronomy, mathematics, and several languages. While no parent would advocate leaving students entirely on their own, you can show sons and daughters how to learn independently, and how to continue doing so long after they leave home.
The classical model emphasizes the arts of learning so that students become lifelong learners. Throughout the Challenge programs, students build on these practices: creating timelines and research notebooks, presenting their research to classmates, debating and speaking, and leading their seminars through Socratic discussion.
You can utilize the Words Aptly Spoken Childrenās Literature: An Introduction to Literary Classics for Challenge A and B to facilitate conversations about the books they are reading through review questions and topical analysis.
Find all the Challenge A and Challenge B literature at the CC Bookstore
Challenge I and Beyond: Freedom, Civilization, and What It Means to Be Human
Challenge I books and short stories center on American history, with an emphasis on freedom versus slavery, civilization versus savagery, and the deeper question of what it means to be human. Not only that, but what it means to be human in America, flaws and all.
The real questions to put to ourselves are these: How do we motivate our students to want an education badly enough to really apply themselves, as Nat Bowditch, Thomas Jefferson, and many others did? What did the people of 18th-century America have that made them believe that one could, and should, educate oneself?
There is no easy answer. It certainly goes against a culture of passive learning and “edutainment,” the idea that a student takes in information as long as it is amusing. But the classical Christian tradition answers these questions differently. Is education only a ticket to higher wages? Or is it the thing that will ensure our freedom, prepare us to discern what is right and good, and help us know God more fully and know how to glorify Him? In the classical Christian tradition, the answer to the first question is no, and the answer to all the remaining questions is yes.
Read Amusing Ourselves to Death
Frequently Asked Questions
What is the Classical Conversations Challenge program?
The Challenge program is the homeschool curriculum of Classical Conversations for students ages 12 and up. Organized into levels (Challenge A through Challenge IV), it uses a Socratic seminar approach to help students engage with great books, develop the rhetoric arts, and grow as independent thinkers and leaders.
What is my role as a CC parent in the Challenge years?
Your role shifts from drill instructor of memory work to mentor and conversational guide. Rather than teaching content directly, you read the assigned books alongside your student and facilitate deep discussions about the big ideas they contain.
How does the Challenge program prepare students for college and life?
Challenge trains students in the arts of learning, including research, rhetoric, Socratic discussion, and self-directed study, so they become lifelong learners. These practices prepare them for college academics, leadership in their communities, and faithful engagement with the world.
Preparing Your Student for Leadership: At Home, in Church, and in the World
These are the conversations we need to be having with our Challenge students, not just once as a pep talk, but often. Each book in Challenge can help us return to these questions. Thinking through big ideas in the safety of your home, with your guidance, is part of the CC homeschool program for high school that prepares your student to handle the conflicts that will undoubtedly arise in their lives as future leaders.
Remember that our children are royalty: they are the princes and princesses of our God, who is King. They deserve an education that prepares them for leadership. Even if you do not think your children will be leaders in public office, they will lead at home, in church, and in their workplaces. Prepare them to lead well, just as Thomas Jefferson was prepared: through conversations about the big ideas.
Keep the conversations going. Read the books. Mentor your children. Together, you both can rise to meet the challenges.



